


the sixth email

by sethLikesTuna



Category: Supernatural
Genre: Alternate Universe - College/University, Anal, Bottom Dean, Emails, Gay, M/M, Masturbation, Nudes, Oral, Professor - Freeform, Professor AU, Top Cas
Language: English
Status: In-Progress
Published: 2021-01-13
Updated: 2021-01-19
Packaged: 2021-03-17 23:36:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,742
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28733574
Author URL: https://archiveofourown.org/users/sethLikesTuna/pseuds/sethLikesTuna
Summary: Dean accidentally sends something that he is not supposed to send to his professor.ORwhere professor Castiel tries not to jerk off to something his student sent him
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Comments: 9
Kudos: 73





	1. chapter 1

Professor Castiel stared at his laptop silently as the sounds indicating he got a new email rang one after another not stopping until the 10th email. He sighed and pressed his hand to his face because he knew exactly what was happening. The professor has told his students today about an assignment due on March, it is January now. But of course, Winchester who has taken a class with the same professor before, will do his work the same day as the announcement, and it would be a mess, and because it would be a mess, the student will notice every minute a new mistake, fix it, then send the work again. Today he sent it 7 times and professor Novak is cursing himself for existing and becoming an educator because of course he’ll meet this kind of very weird students.

Castiel took his hand away from his face, directing it to his coffee cup while inhaling and exhaling softly. He took a sip, placed his mug back on his desk and cracked his knuckles “alright, you can do this Castiel” 

He started going through the emails from the oldest one sent.

“Good morning professor Novak, how are you? I have finished my assignment and I am aware that the due Date is two months away, but work would probably be stacked up by then and I thought why not give you one less problem? -Dean Winchester” 

file attached 

Castiel rolled his eyes “one less problem? You’re a whole new set of a 99 problems” he mumbled then existed the email not looking at the document attached because he knew it wasn’t the final one so he moved up to the next one. 

“I am sorry Dr. Novak but I had forgotten to conclude my research, this is the final document. –Dean Winchester” 

Castiel scanned the email sent to him but he couldn’t find any documents. He sighed then moved to the next email. 

“I am extremely sorry I have forgotten to attach the file of my assignment, excuse my clumsiness. I apologize again. –Dean Winchester” 

file attached 

Castiel found himself giggling at the email but he stopped himself immediately before smiling warmly at the clumsy boy, he did not want to reward unprofessional behavior that gives him a headache, even when no one is looking. The professor scratched his eyebrow then comforted himself “three down, four to go” he clicked then on the fourth email. 

“the version I have just sent you is the version I first made without a conclusion I am extremely sorry I do not know what is wrong with me and I am extremely embarrassed with myself, here is the final one. I am sorry again. –Dean Winchester”

file attached 

Castiel furrowed his eyebrows and hid his face in his hands again. He was thinking if Dean is alright. How is he like this? Why is he like this? How does he get with his days? How didn’t he die when he was a child? How did he survive with such a brain? And why must Castiel be its victim? 

He sighed for the thousand time today and took another sip of his coffee to move to the fifth email.

“um so, I realized I accidently deleted the last paragraph while adding the conclusion, I am very very sorry and I promise you this is the last email I am sending. –Dean Winchester”

no document. Castiel cursed and opened the sixth email 

“I am sorry I forgot to add the document AGAIN. Can you imagine how stupid one might me to forget to add a document for the second time after sending them five emails? Haha. I am sorry again, have a good day. –Dean Winchester” 

file attached 

The sixth email annoyed Castiel a little, he didn’t know why but dean calling himself stupid offended the professor. Yes, of course Castiel thought to himself countless times before that Dean’s an idiot, but Dean shouldn’t think that about himself. Dean was one of Castiel’s smartest students, he took a course with him when he was just a freshman and he got an A+, in fact he was the only one. Not only that but he’s also in his senior year at the age of 23 and he’s going to graduate this year, before his other colleagues who major at philosophy too and started with Dean. Dean’s not stupid, he’s just distracted. The professor told himself before opening the seventh email. 

“oh my god I am extremely sorry and extremely embarrassed I did not mean to send that to you, I just received these documents now via email and accidently put them instead of my assignment, this was not intentional whatsoever. It was an honest mistake I did not mean by it anything I promise you. I will drop out of your class if you’re disgusted by it and I’ll never show my face here ever again just please do not report me to the administration of the university I am sincerely sorry. –Dean Winchester” 

The professor knitted his eyebrows and opened his mouth slightly being extremely confused and concerned. He stared at the email for almost five minutes and kept rereading it then rereading the name of the sender. He took in a sharp breath then went back to the sixth email. The professor pointed the mouse at the document debating if he should or should not open it. He circled around it hesitantly, he knew he shouldn’t open it, it is obviously something not meant for his eyes but he was also so curious to know what could have made the student think that Castiel would be extremely offended by, he wanted to know, he had to know. So he took a last breath and opened the document which turned out to be three pictures, he opened the first one and holy shit, it was a very high quality picture. 

Castiel’s jaw dropped as soon as he saw the picture open up on his laptop. It was a picture of Dean, it was clear that its photographed professionally. It was from the point of view of someone above Dean’s naked body. Everything was visible, his half lidded green eyes, his freckles on his flushed cheeks, his parted plump glossy lips, it was obvious that they have just been sucked. His messy hair, his freckled chest where his swollen nipples were erected, also the hickey beneath his right nipple and the one on his neck. His exposed toned stomach, his strong parted thighs that were also filled with bruises, and finally his big flushed and erect cock that was leaking precum, it had the professor’s mouth watering. 

Castiel blinked few times trying to comprehend the fact that he is looking at a nude picture of his student, that was accidently sent to him. Of his nerd, clumsy, idiot and hardworking student. He gulped and moved his eyes at every corner of the picture unconsciously. He did not want to look but couldn’t take his eyes away and started thinking about the other pictures. It’s not right, he shouldn’t look, is what he kept saying to himself as he opened the other picture and holy shit, it almost gave the professor a mini heart attack. 

It was from the point of view of someone who was standing up, and being sucked by Dean. He was on his knees on the floor, his pink lips were around the tip of the dick and he was looking up at the camera. Castiel swallowed hard, he never thought that dean was into men, he never looked like it according to the professor’s stereotyped characteristics of a man loving man, but that wasn’t the thing he was concerned about, he was concerned about the blood that was traveling to his penis, causing him an erection. He had to stop now, he had to turn his laptop off and forget what he saw he really had to, but somehow the third picture was opened. Dean’s head was pushed against the pillow with a muscular arm. His ass was lifted up and another muscular arm was spreading Dean’s red ass cheeks to show his spread open pink hole that was leaking cum out of it. The professor’s arm lowered to his crotch and he gave himself a squeeze through his slacks and let out a low groan. “oh shit” he mumbled to himself as he quickly stood up and shut his laptop off. He walked in circles in his home office not knowing what to do and feeling embarrassed himself. The erection in his pants only grew harder and the pictures did not leave Castiel’s head. He wanted to jerk off and relief himself but he did not know how he’d live if he jerked off to one of his students, it was unethical and wrong. 

The professor sat down on his chair again trying to ignore the uncomfortable and painful boner in his slacks that wants to break free. Castiel decided he would not do anything regarding his dick and he will continue working until it goes down in itself, so he opened his laptop and the first thing he saw was of course Dean’s exposed ass. His cock twitched and Castiel quickly existed his email page to go back to his desktop. He took a sharp breath and then opened the e-book he has for another course he lectures, to highlight some important things that he needed to lecture for next class. 

Five minutes passed and Castile did not highlight shit. His boner isn’t chilling and the pictures of Dean turned into videos in his head. He pictures those sweet lips around his cock and that the cum leaking out of his ass was of his professor’s cock. He imagined how he’d take him right on his office table, how he’d moan, whine and call out his sir’s name.  
Castile couldn’t take it anymore, he placed the laptop on his knees and opened the first picture of Dean. He quickly unbuckled his belt and opened his flyer then took his throbbing cock out. He immediately started stroking his length while never taking his eyes off of Dean. He held his hard penis with one hand and with the other he held the laptop’s screen, stroking his thumb at where his student’s cheek is. He then switched to the second picture where Dean is sucking someone off, someone that Castiel was very jealous of. “oh fuck- Dean” he moaned while closing his eyes now, imagining that he’s fucking the student’s mouth. He was reaching the edge now so he switched to the last picture but before he can picture himself spreading Dean’s ass open he orgasmed and his cum splattered against his laptop screen and in Castiel’s head, his cum looked way better on Dean’s ass than this stranger’s semen.

After he cleaned himself he found himself typing an email “You still did not send me your finished assignment. –professor Castiel Novak.”


	2. chapter 2

Dean was drinking his seventh shot of pure vodka when he received an email from his professor Novak. He has been so embarrassed by what he has accidentally sent that his anxiety just went over the roof and he drowned himself in alcohol, it seemed like the only logical thing to do. He had cried a little, not because he might get kicked out of college for sexually harassing a professor, when he is so close to graduating, but because he respected the professor a lot and looked up to him. He always imagined that one day he’d become a professor just like Novak. He’d wear the same suites that his blue-eyed educator wears, and he’d be so kind and helpful to his students just like professor Novak. Dean always wanted to please the professor and show him how good of a student he is, he worked a lot to get full marks on his exams, and did his assignments as soon as possible to not trouble Novak. He loved it whenever the professor praised him and told him “good job” “excellent work” “that’s a very smart question, Winchester” 

And now he has sent nudes, not only nudes, but sex shots of him sucking cock and having cum leaking out of his ass to his role model. Dean cursed his friend Charlie for suggesting he takes the job and model for a porn website, well he did need the money but if he knew the consequences to it he would have not done it. When he realized earlier that the document he sent to his professor was the pictures, he sat down on the floor and cursed a lot while imagining the disgusted look on Dr. Novak’s face.

Dean stumbled on his dorm room to his laptop that was located on his bed, trying not to knock down anything. He saw the he got a new email and his heart dropped when he saw it was from professor Novak. If he was sober, he would have been too nervous to open it and would wait almost 15 minutes before doing so, but he was hammered, so he gulped and opened it immediately

“You still did not send me your finished assignment. –professor Castiel Novak.” 

Dean’s eyes widened after he read the email and he was relieved, only a little though, because it did not seem like his professor was going to report him. but nothing ever erases the fact that his professor saw him in that state. 

Dean’s brain was a mess, but he also drank a lot of alcohol and he was drowsy. He replied to his professor’s email

“sory abt it here si the asignmet –dean winc” 

and he obviously, did not attach the assignment. 

\---

Dean took deep breaths, and tried to relax himself as much as possible, he did not have the courage to walk in that classroom where professor Novak is going to lecture him, he couldn’t show the man his face. He was already five minutes late, and that never happened before, he always was punctual and coming late would indicate to the professor that something is wrong and that would make things awkward. Dean needed to act normal and pretend that nothing happened but he found himself debating if he should go in or just run back to his dorm. He was overthinking everything, where would he sit if he went in? he always sits in the front raw, but he really does not want to show his shameful face to professor Novak but by not doing so he would break his rule of pretending that everything is normal.

Dean took a last deep breath and decided to go in. Him being late wouldn’t be a problem since his professor does not give a rat’s ass about attendance. He believes that no one should force anyone to learn, and if someone believed that they did not need the lectures to understand the material of the course, then they are free to not come, and Dean truly respected that. 

Dean walked in and glanced at the professor who has already started lecturing, the professor glanced back at him and Dean quickly looked down and proceeded to take a seat in the front raw. He took out his notebook, not to write notes, he used his laptop for that, but to doodle because it was one of his ways to handle stress and anxiety when people are around. 

The professor was lecturing and asking questions that Dean knew the answers to while no one else did, but he did not answer them, he kept on doodling and he never once looked up from his notebook until the lecture finished. 

“Alright, so that’s all for today, if you have any questions you already know my office hours, see you guys next week. oh, and Winchester, would you mind staying a bit or do you have a class to attend?” 

Dean’s heart started to bound quickly, he looked up and nodded “yes, I mean no, I mean I do not have a class after this one, I can stay”

The professor smiled at him and sat at his desk as students started to get up and leave. some of them went over to his desks to ask him some questions, Dean just sat nervously waiting for everyone to leave. He wondered what the professor wanted from him, scold him? tell him how disgusting he is? Blackmail him? Dean counted the students left in class as they walk out until the last one left.

He looked up at his professor who smiled warmly again “come here, Dean” Dean bit his tongue and felt his stomach fluttered because this was the first time that his professor called him with his first name. Dean got up and stood in front of Dr. Novak’s desk. 

“so..” the professor started but Dean cut him off “I am extremely sorry, I know that offended you but I swear it’s not what you think it is, I needed the money and the photographer emailed me the photos while I was trying to submit my assignment. I am sure that was disgusting for you and-“ 

now it was the professor’s time to cut him off “stop it, Dean.” He demanded and the student stopped rambling and looked down. Dr. Novak sighed and continued “I understand, a mistake like this can happen, do not beat yourself too much about it, alright?” Dean quickly looked at the professor’s face, he did not expect the professor to say that. “I am just concerned for you, look, you did not interact in class today whatsoever and you did not seem to be focused, and I am afraid that this incident would affect you academically. You are a very bright student Dean, and you have so much potential. I do not want you to drop out of this class because it will miss up your graduation plan. You have come so far and I am very proud of you, don’t mess it up now” 

Dean stared blankly at his professor, he did not expect this at all. He did not know how to respond to that but his eyes watered a little, though no tears rolled down, no matter how much they wanted to. All his life, Dean worked hard, for himself and his little brother with only little help from his uncle Bobby. he worked very very hard, he studied a lot and did tens of part time jobs, and this is the first time anyone have ever told that they’re proud of him.

He blinked the tears away. of course, that’s what his role model would say to him, of course he is one of the kindest and most helpful people Dean has met, of course he wouldn’t let some disgusting pictures stop someone’s education. 

“yeah sir, I am sorry I just got a little embarrassed and anxious, thank you a lot for not letting that change your perspective of me” 

the professor exchanged his smile with another one “what you do in your personal life is none of my business, all I care about is that you’re a good student” he said as he stood up and started collecting his stuff “alright now that we got that out of the way, see you next week, alright?” he looked at Dean who nodded at him. 

he then walked away and before he existed he looked back again “and Winchester, you still did not submit your assignment” and left

Dean’s cheeks heated up, now that’s really embarrassing, Dean is as forgetful as a goldfish. he put up a mental note in his head to submit the assignment as soon as he returns back to his dorm room.   
\---

After an exhausting day Dean plopped over his mattress, finally back to his dorm room. He looked up at the ceiling and immediately smiled when he remembered what his professor has told him. “I am something to be proud of” he mumbled to himself and his smile grew wider. He remembered Dr. Novak’s smile as will, it was warm, assuring and loving. His white teeth, his full lips, the wrinkles that appear besides his eyes when he smiles, his big hands and thick fingers, his- 

Dean stopped his train of thought and his smile disappeared. ‘what the fuck are you thinking of?’ he thought to himself, but then he remembered again the words that his professor told him. somehow “good student” was translated into “good boy” in Dean’s head and he couldn’t help but blush when he imagined it coming from his professor’s lips. He covered his eyes with his arm and tried to make his dick chill down a little by ignoring the blood rushing to it. But the words really didn’t leave Dean’s head “I’m such a good boy” he moaned to himself as his dick twitched in his pants “so good for you professor Novak” 

His whole face turned red and he licked his lips as he pictured the professor’s naked body. His mind repeated to him that he shouldn’t do this, he shouldn’t look at his role model like this. But his arousal was insane, he didn’t know that praise can do things to him like this, he knew he liked the professor a little bit more than he thought, even if he didn’t admit it to himself. He always fished for his approval and pleasure, the days he praises him would be Dean’s best days and his good mood would be unbreakable. Even in some one night stands, Dean’s sex partners did praise him, but it did nothing to him. When his professor praises him, he knows that he means it truly.

His hand was now under his boxers, stroking his hard penis while calling out his professor through moans and needy whines. “fuck, professor, f- fuck” he pictured the professor fucking him senseless. The view of his professor was slowly becoming more and more vivid and Dean’s orgasm was building up fast, he wanted to be touched and felt by the older man so much, he wanted him to praise him in a proper way, show him how proud he is of the student. 

Dean stroked his cock through his orgasm, and he came calling out his professor. When he finished he picked up his phone while panting and typed out a text to his friend Charlie “something happened, I think I’m fucked. I don’t know what to do”

**Notes for the Chapter:**

> stay tuned for chapter 3, the last chapter.

**Author's Note:**

> stay tuned for part 2!


End file.
